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From Zero to Sailor: A Quick Guide

5 years ago, everything I had fit in a pack. I decided I was tired of hopping trains and hitching, and wanted to become a sailor. Practically everybody told me it was impossible (except, ironically enough, actual sailors). I had never set foot on a sailboat in my life. I had no money, and boats are expensive. A year later, I was sailing my own boat. This is a quick guide for people that want to get into boats, but have nothing. It pretty much comes down to three steps.

#1: Get a Boat.
Don't get one that doesn't operate. You need one that is good to sail, and ideally one that has a running motor. Project boats will suck up all your time and money, and there's a good chance you'll be forced to give up on it before you ever get sailing. The good news is that boats can be way cheap to buy, or even free, if you're smart. In some areas, the market for used boats is saturated, and the cost of storing a boat is extremely expensive. This means people will sell good boats for dirt cheap, or occasionally just give them away. I paid $4,000 for a fully working 26 foot sailboat, and obtained another 25 foot sailboat for free (no motor, gave it to a friend who slapped a $500 outboard on it).

The area I went to was San Francisco. A slip in the bay area for somebody living on their boat is $800/month at the very cheapest. So every month that somebody takes to sell their boat is $800 out of their pocket. I began shopping in the winter, which is the time when people are most desperate, because nobody's buying boats in winter. Craigslist is your best friend when you're shopping; you can even set it to e-mail you whenever new search results pop up. Craigslist e-mails me whenever a free boat pops up in the bay area, so I'm aware within 15 minutes. By that time, the person who put it up has probably already had 5 responses. You have to be quick, and you have to be ready to go get it right then. Free boats that are worth it are extremely rare; it's usually not worth it if you have to fix it. You're better off with a bit of money in your pocket; I've seen fully working 30 foot cruising-ready boats go for less than 5k. Sailboats are not free to operate; new sails are $1,500 and up. Even used sails can be $500, and the bigger your boat, the more expensive it is. You want fiberglass, not wood, not steel. Wood rots, and everybody I've known with a wooden boat has spent a lot more time repairing it than sailing it. Steel rusts, and unless you happen to be an experienced welder, you won't be able to afford maintaining it.

#2: You Need to Put Your Boat Somewhere
This is extremely important. A slip can be expensive; you get charged more just for living on your boat, and the process of not getting caught can be difficult if you try to avoid that fee. The slip my boat came with was $500/month, with an extra $300 if I wanted to live on it, for a total of $800. Anchoring is a solution, but many places are eliminating public anchorages, making choices slim in some areas. In the bay area, there was only one public anchorage left when I got my boat, which is Richardson Bay in Marin county. This is a great option, except when the wind starts blowing. Two days after I first put my anchors down, the wind was howling at 70 miles an hour and 6 foot swells were slamming into my hull...for 4 days and 5 nights straight. I've had boats run into me, snag on my anchor lines, I had a boat full of yuppies run into my anchor lines and cut it with their motor, I've been pretty certain I was going to die a few times. And out of 200 people living out there at anchor, 75% of them are tweakers who will happily rob you of anything of value, including your very oars that you use to get to shore and back. If it's worth $20, they will steal it, and if they can get into your boat, they will rob it.

Suffice it to say that after three years at anchor, I do not recommend it. Sometimes, it's amazing and glorious, but I've seen uncountable boats go to shore (my own, eventually), and the death rate was comparable to the train hopper community. The first week I spent at anchor, 14 boats went to shore. Unfortunately, you're going to want income while you're living on your boat. You may have to job up.

#3: Sailing is Easy
Seriously. It's really not hard. After a couple of lessons, you should know the basics. Make the person who sells you the boat throw in a couple of lessons. It can be hard finding people to take you out if you don't know anything, but if you hang out in a seaside town and chat up enough people, eventually you'll find a sailor who's going out and doesn't mind alternafolk. Trying to get random people at docks to take you out for a sail will likely be pretty difficult; very few people are willing to take a random inexperienced stranger out with them. You may have to take a shower and put on some clean clothes. Once you know how to tack and how to gibe, you can sail a boat. There's a lot more to learn to be GOOD at it, and to be able to make an ocean passage, but that's why you spend time practicing and learning. The important thing for me was that it becomes a lot easier to practice and learn when you have a boat. You wind up networking with other sailors, and going out on their boat, and taking them on your boat, and you learn to use a bunch of other kinds of boats and they show you things you didn't know about your boat.
 
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iamwhatiam

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Thanks for the post. I really like the advice especially in #1. I've known several people who bought a fixer upper on the cheap cheap thinking they were saving money, but then never even left the marina/moorage when they realized how much $$ they'd have to put in to it to get it seaworthy. (It seems like more often that not, while fixing one thing you discover another thing and another thing that needs fixing) And a boat that just sits there and never sails is one of the saddest things IMO.....like a dusty guitar in the corner of the room that never gets played.

I'm actually looking for a boat to learn on around the Puget Sound. Smaller boat now, then upgrade to bigger one for long-distant voyages later once I get some experience under my belt. I think I've narrowed the boat down to a Catalina 25. Most I've seen in the area are around 5 or 6k in decent shape and they come with a trailer and motor. Easy to find parts, big catalina community online, and I'll have a trailer to move it when it's not in the water.

If anyone has any experience sailing Catalinas, I'm all ears. Hoping to find my boat by springtime.
 
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Dameon

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Catalinas can be pretty decent boats, but I'd personally go with 26-28 feet as a minimum, and not really get caught up on brand. At that size, a sloop is mostly a sloop, and will mostly sail the same, but you'd be amazed at the difference one or two feet can make. Oh, and you want a cruiser, not a racer; that can make a huge difference in livability.
 

freegander

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thanks for the post! everyone i've talked to seems to think sailing is real difficult, but the more i read about it, the easier it seems.

what boat do you have and where have you sailed to? or are you still learning the ropes?
 
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Dameon

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I'm actually boatless at the moment, while I pursue land opportunities to make enough money to really get going internationally. My boat was an S2 8.0b, and I sailed it all around the San Francisco bay, which is huge, and some of the most challenging sailing in the world thanks to extremely strong currents, rapidly changing winds, and lots of rocks and other vessels. The hard part of sailing isn't the sailing itself, it's handling challenges and emergencies, and endurance, and learning how to live and work in small, tight quarters. The sailing itself, I could teach anybody in 30 minutes of hands on time.
 

freegander

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Wow, that's incredible! I'm really inspired that you could live aboard a boat that long and learn how to sail without spending loads of money.

I'm currently in the same boat (heh heh), saving up for a rig so i can travel internationally. how much do ya think you might have to save?
 
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I'm currently in the same boat (heh heh), saving up for a rig so i can travel internationally. how much do ya think you might have to save?
I'm going for at least $10k, I know I can get a 32+ foot boat for about $5k that's good to go, and I can get pretty far off another $5k, plus I'll be making money along the way (I'm hoping to leave with more like $20k). Getting a used boat is relatively cheap, but maintaining them can be pretty expensive. $1k for bottom paint, $2k for a new sail, $500 for a winch. Some of the costs can be reduced by knowledge and effort, some can't.
 
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Dameon

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how long do you think that will last you for? i am guessing i could survive at around $500/month easily, but that's based on my van travels. i have no idea what expenses life at sea could entail
It's a really tough call, depends on any number of things like what breaks (which can depend on how hard you push the boat) and where you are when it breaks (a winch in the UK might not be the same price as a winch in the Caribbean), where you buy your supplies, and all that. Fuel can be pretty pricey, especially outside the US, so how much you run your motor figures in. And of course, if you're at sea, you're not going to be spending hardly anything.
 
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very helpful stuff i learned a lot from this thread
 
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Dameon

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are you required to have insurance on a sail boat?
Generally, not by law (there might be some states that are exceptions, but I'm not aware of them), but marinas require you to have insurance if you want to get a slip there. It's very cheap compared to car insurance, though, just a $100-$200/year.
 

Road warrior

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Great story, I love sailing. My brother was an avid sailor in Hawaii and showed me the ropes of sailing. It was an amazing experience for me.
The best adventure was heading towards Diamond head, we were healed over and saw the sailboarders that found this area the best.
I would love to be in the flotilla that sailes from Vancouver B.C. to Hawaii...
Once you've sailed once you're addicted, the best adventure imaginable...
 

Dirtdog84

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That was the only time I was ever happy I lived on a 22 foot fishing boat. Ugly as fuck but I was happy as one can be. Just me and my dog on that tiny boat.
 

Poptart

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Ive been saving for a 32ft boat for learning and eventually going international. I'm Definitely looking for lessons if anyone experienced reading this; I get carried away looking at all the Craigslist/free-boat ads.

how do you keep your boat on lock down and the scavengers out when you're not on board?
 

BirdDaddy

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are you required to have insurance on a sail boat?
also consider the money your dumping into it and the risk compared to a car. i feel i would feel generally more comfortable learning knowing that at least half my fuckery could be covered. especially theft or vandalism. seems to me a boat at dock or anchor is pretty vulnerable to unwelcome guests. i mean im certain insurance on a boat is just as if not more scandalous than on a car. i mean less regulated and all.
 

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